5-chloro-2-(2-cyclohexenylthio) benzothiazole



United States Patent 2,992,227 S-CHLORO-Z-(Z CYCLOHEXENYLTHIO)BENZOTHIAZOLE John J. DAmico, Charleston, W. Va., assignor to MonsantoChemical Company, St. Louis, Mo., a corporation of Delaware No Drawing.Filed Nov. 19, 1959, Ser. No. 854,018 1 Claim. (Cl. 260-306) Thisinvention relates to S-chloro-Z-(Z-cyclohexenylthio).benzothiazole whichmay be prepared as follows: To a stirred solution comprising 50.4 grams(0.25 mole) of S-chloro-Z mercaptobenzothiazole, 40 grams (0.25 mole) of25% sodium hydroxide and 250 ml. of water was added in one portion 40.3.grams (0.25 mole) of 3- bromocyclohexene. An exothermic reaction set incausing the temperature to rise from 25 to 48 C. After stirring at roomtemperature for 24 hours, 200 ml. of water and 300 ml. of ether wereadded. The ether solution was separated, washed with water until neutralto litmus and dried over sodium sulfate. The ether was removed in vacuoat a maximum temperature of 80-90 C. The product was obtained as anamber oil in 81% yield. Analysis gave 4.7% nitrogen and 22.2% sulfur ascompared to 5.0% nitrogen and 22.8% sulfur calculated for C H ClNS Theproduct is both a contact herbicide and defoliant. These usefulproperties were demonstrated by applying5-cl1loro-2-(Z-cyclohexenylthio)benzothiazole in spray form to thefoliage of grasses, to the foliage of bean plants and to the foliage ofa mixture of broadleaved "Ice plants and observing the phytotoxicity. Inthe table below, 0 indicates no phytotoxicity, 2 moderate phytotoxicity,3 severe phytotoxicity and B indicates defoliation. A concentration of0.5% of the active ingredient was employed.

Table Grass Bean Broadleai' Mixture Mixture 5-Oh1oro-2-(Z-cyclohexenylthio)-benzothiazole 2 3+B2-(Z-Oyclohexenylthio)benzothiazole- O 0 30 B defoliation.

References Cited in the file of this patent FOREIGN PATENTS GreatBritain Feb. 6, 1957 OTHER REFERENCES Moore; Chem. Abstracts, vol. 47,col. 10523 (1953).

